Structure Revision of the Sesquiterpene Nordine Based on NMR Spectroscopic Analysis and X‑ray Crystallography

Nordine was reported to be an unusual humulene-type macrocyclic sesquiterpenoid that contains an ether-bridged bicyclic ring between C-10 and C-6 with a hydroxy group at position 2. Here, we report the structure revision of nordine based on incongruities found for carbon chemical shifts in the origi...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2022-10, Vol.85 (10), p.2480-2483
Main Authors: de Andrade, Rodrigo Silva, Sales, Kaio Aragão, Abreu, Lucas Silva, Campos, Vinícius Rangel, dos Santos Junior, Fernando Martins, Braz-Filho, Raimundo, Scotti, Marcus Tullius, Tavares, Josean Fechine, da Silva, Marcelo Sobral
Format: Article
Language:English
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Summary:Nordine was reported to be an unusual humulene-type macrocyclic sesquiterpenoid that contains an ether-bridged bicyclic ring between C-10 and C-6 with a hydroxy group at position 2. Here, we report the structure revision of nordine based on incongruities found for carbon chemical shifts in the originally proposed structure, in addition to formation of a diacetylated derivative. As expected, a single-crystal X-ray diffraction analysis unambiguously confirmed our proposal that the nordine (1) structure contains an ether-bridged bicyclic ring between C-10 and C-7 and hydroxy groups at C-2 and C-6. Furthermore, the absolute configuration was determined by ECD spectroscopic analysis.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.2c00828